Hydrochloric Acid → 1-[(4-Methoxyphenyl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehyde

HRID 554168Notes

Reaction equation

HRID 554168 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:15][C:14]([C:23](OCC)=[O:24])=[CH:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:15][C:14]([CH:23]=[O:24])=[CH:13]2)(=[O:10])=[O:11])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 66924572Ethyl 1-[(4-methoxyphenyl)sulfonyl]-5-phenyl-1H-pyrrole-3-carboxylate

Product 1

HCID 862329231-[(4-Methoxyphenyl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehydeYield 65.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Ethyl 1-[(4-methoxyphenyl)sulfonyl]-5-phenyl-1H-pyrrole-3-carboxylate (430 mg) was dissolved in tetrahydrofuran (10 mL), and the mixture was cooled to −78° C. A 1.5 mol/l solution (3.36 mL) of diisobutylaluminum hydride in toluene was added dropwise, and the mixture was further stirred at −78° C. for 1 hr. 1 mol/l Hydrochloric acid (20 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in acetonitrile (10 mL), tetra-n-propylammonium perruthenate (39 mg), N-methylmorpholine N-oxide (227 mg) and molecular sieves 4A powder (500 mg) were added, and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was suspended in ethyl acetate and filtered through celite. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→1:1) to give the title compound as a brown oil (yield 249 mg, 65%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in acetonitrile (10 mL)
  6. additiontetra-n-propylammonium perruthenate (39 mg), N-methylmorpholine N-oxide (227 mg) and molecular sieves 4A powder (500 mg) were added
  7. stirringthe mixture was stirred at room temperature for 30 min
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. filtrationfiltered through celite
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customthe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→1:1)

Sources & evidence

ORD record
ord-bf9ee9233abc4483b86071427edcb2b6
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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